I’ve been circling around a topic for this week’s newsletter until I noticed a little theme in my latest journaling (I love when that happens!)

I keep coming back to this idea of betting on yourself, and why it matters so much when you’re building something. Whether you’re starting a podcast or launching a business or putting yourself out there in any way, you have to be your biggest advocate from day one.

But what does that actually look like?
Is it just a mindset? Or does it require an actual investment of time, money, or energy?

As an entrepreneur, it can be easier to feel like, "I need to avoid expenses at all costs." I actually ran my business for the first couple of years that way, thinking a responsible solopreneur business meant not spending any money.

I’d resist upgrading software, skip courses or coaching, and try to figure everything out myself.

Earlier this year, I decided to do things differently (something I’ve written about previously). If I’m studying what successful businesses have done before me, the pattern is clear: they know when to get help and they treat investment as part of growth. Inspired by this, I’ve made it my goal to build systems that let me feel like A) the business is more stable and B) I can invest in the software/programs etc. that will help me get to the next stage. Which led to:

→ Joining The Hearth in London, my first full-time co-working space and a surprising source of new ideas and connections.
→ Paying for tools that save time (beehiiv, wispr flow, and others) instead of defaulting to the free tier.
→ Creating more financial stability so I can build long-term instead of chasing short-term fixes.

In this week’s newsletter, I’m going to explore investing in yourself from different lenses: the practical ROI (investing time/money/energy), the opportunity ROI (how raising your hand & building in public attracts opportunities, and the creative ROI (how creators can turn self-believe in to a lasting media business.

This ties in perfectly with my latest Creator Diaries interview with Taylor Harrington, who’s built a career around community and helping people find belonging online.

I talk a lot about the power of putting yourself out there and creating content online, but it’s easy to forget the tactical side of how you actually do it. How do you build a personal brand around the things you really love? How do you form real relationships while doing it? All of those things are equally important and they’re central to Taylor’s work.

She’s the Head of Community at Dreamers & Doers, a group for women entrepreneurs, but she’s long been active in the community space and even got her start working for Seth Godin. She’s seen the early evolution of this creator–entrepreneur overlap up close and has such thoughtful insight into how you build your brand to attract opportunities.

The advice that stuck with me most from our conversation is something she learned while working under Seth: “Don’t wait to be picked. Raise your hand.”

Taylor’s story is proof that opportunities start from that one small act of self-belief.

Her energy throughout our conversation was contagious, and it made me think about how this idea of betting on yourself is decision you make every time you hit publish, send a pitch, or put your next idea into motion. 💫

Read the full Q&A here

Betting on yourself used to mean starting a business. Today, it can also mean starting a brand, a newsletter, or even a modern media company built around your voice.

I’ve been mulling over the future of creator-led media because it feels like the place where all my interests intersect - the creator economy, the rise of personal brands, and my background in media businesses.

In every newsroom or media environment I’ve worked in, there’s been some version of the same challenge:
→ Ad models that no longer work the way they used to.
→ Audiences that feel impossible to hold onto.
→ Leadership that knows change is needed but struggles to make it happen fast enough.

And yet, people are consuming more content than ever. They’re just finding it in new places, from creators who are building media brands around their own voice, values, and curiosity.

That’s why I’ve been fascinated by The Free Press acquisition. Regardless of your view on Bari Weiss’s editorial angle, the takeaway is clear: she built a media company from scratch, fueled by her own credibility and a direct line to readers. It’s proof that you can build something meaningful around ideas you care about.

This model is simple, but it works:
→ Build distribution through your personal brand.
→ Create content that people actually look forward to.
→ Own your relationship with your audience (newsletter, community, direct channels).
→ Add revenue layers—paid content, partnerships, or products that fit naturally.

That’s the creator business blueprint👇

I find this SO exciting because the doors are wide open to build a business you love. You can literally open your laptop, start publishing, and within a few years, have a business that supports your life. Something meaningful, profitable, and entirely your own.

This reminds me of a great essay by Nathan Barry, the CEO of Kit, called the Audience Shortcut. In it he argues that opportunities come from building the right audience.

The more you put yourself out there & build an audience, the more opportunities come your way. And on the flip side the risk of starting something new decreases with every increase in audience size.

Reading back over Nathan’s essay I was reminded how on theme it was to betting on yourself and my conversation with Taylor. As he writes, “being someone who is actively pursuing their dreams and sharing the journey puts you in rarefied air. You will stand out, as that’s just 1% of people.

This is where I want to help - to push and inspire other people to join that 1% of people building something they love. If I can play even a small part in helping more writers, creators, and entrepreneurs build six-figure businesses around what they love, that feels like the DREAM.

Before we wrap up, a quick recommendation I’ve been loving lately: The Department podcast by Omar El-Takrori.

I stumbled on it a few weeks ago and have been binging episodes ever since. Omar talks about building your personal brand from the perspective of an entrepreneur - how to sell your knowledge, package your expertise, and create systems that actually support growth.

A few episodes I’ve bookmarked:
→ How To Sell Your Knowledge and Make More Money Online (Russell Brunson)
→ How To Become A Millionaire in 2025 (Using AI) (Dan Martell) *a little too clickbaity of a title for me… but the advice is solid
→ How To Make Your Personal Brand Stand Out in 2025

If you’re in a season of rethinking how you invest in yourself - financially, creatively, or strategically - this podcast is worth a listen.